There is not a shortage of stories of gamblers who lose it all, especially today, when gambling addiction is in the limelight just as much as any other addiction.

But there are stories that stand out, stories that show just how much horse racing can have an impact on a person’s life. The stories presented below span centuries, from the days before online gambling, before off the track betting, all the way to modern times. They vary in details, in monetary losses, but there is a running similarity – love of betting on horse races.

The stories prove the pull and attraction of the racetracks, of the pounding of the horses’ hooves, of the crowds, but most of all, the pull of the bets. In these stories, we see how the combined love of horses and betting has led people to their financial, and sometimes even, psychological ruin..

1. The Story of Riley Grannan

Grannan was one of the most common sights at the racetracks from 1888 up until a few years before his death in 1908. He was one of the most famous gamblers and bookmakers of his day, losing, winning, and losing his fortune again and again, in an endless circle until he walked away from the tracks around 1904 for good.

During his time, Grannan was known as a plunger, a term used in the period to describe people who placed seriously large bets, sometimes of thousands of dollars, on the horses. He was also a bookmaker, and reportedly had a good eye for the horses, and often managed to win fortunes. But just as often, he lost. In 1896, Grannan was reportedly banned from the racetracks in New York, due to suspicion that he had bribed a jockey.

In the aftermath, he relocated to Europe, but came back in the US in 1898, preferring the tracks of the Midwest and California to those of New York. Reports of this period, however, show that his big plunging days were over. His final grand bet was in 1903, when he placed an astounding amount of $18.000 at a racetrack in New Orleans and lost. It is not certain that this was the loss that made him walk away from the racetracks for good, and opened a saloon in Nevada, where he died in 1908.

2. Ed Cheeseman – From a Bank to a Prison

Ed Cheeseman was a banker who loved the racetracks, the horses, and most of all, he loved the betting. Back in the 1990s, Cheeseman was at the height of his career as a banker, but lost it all to horse race betting.

His story revolves around the racetracks at Saratoga, where his father would take him when he was young. They would place innocent bets on horses, but towards the end, Cheeseman would spend more than a thousand dollars a day on multiple bets throughout the day. His favorite bet was a $40 exacta box, with $40 on each of the six combos that three horses can form if they finish first or second. In other words, Cheeseman would bet around $240 on a single race, and he would bet on several races in one day.

Before his downfall, Cheeseman worked at the National Savings Bank in Albany for 19 years, and at the height of his career, he was a vice president for commercial loans. Naturally, he had access to a lot of money from investors. He began to think that he could use those to break even and regain his losses.

In that time, according to Cheeseman himself, the Saratoga racetrack was the place to be for bankers, investors, and lawyers. For him, going to the racetracks was a social event, a social event that in turn, fueled his addiction to horse betting. He ended up owing $604,372 to the National Savings Bank, $405,769 of which belonged to clients, who did not know that instead of investing their savings, he was funding his own addiction to horse racing.

Cheeseman never managed to break even, regain the losses and pay back the money he had used from clients. In 1992, the law caught up with him. After standing trial and pledging guilt, he was sentenced to the Federal prison in Pennsylvania.

3. Horse betting leading to ruin in modern times – David Milch

David Milch is the writer and creator of television as we know it today. He created the groundbreaking NYPD Blue, and the incredible television series Deadwood. Milch has enjoyed a career in Hollywood for decades, and has made over $100 million from his television shows and movies, but he has lost it all to horse race betting.

One of his television shows, Luck, which got cancelled in 2012, revolved around horse racing and betting on the racetracks, and Milch himself described it as his “love letter” to horse racing and gambling. Milch has owned a number of horses throughout the years, but he had sold them all back in 2011. However, in between 2000 and 2011, Milch lost over $25 million to horse race gambling, and today, he is over $17 million in debt.

David Milch’s addiction to horse races was not hidden, and his family members and friends have always been aware of it. His wife, Rita Miller, has filed a lawsuit against their financial managers, because she had not been made aware of Milch’s losses and the state of their finances. According to many of his friends, he took to the racetracks with the same focus he showed towards his creations, and he is a very good handicapper. But he would also bet on every race, and spend thousands of dollars on the racetracks, sometimes within one day on multiple races. The Santa Anita racetrack was his place of choice, where he was reported to be a constant presence.

Today, David Milch has an ongoing exclusive deal with HBO, which is talks of renewal. He is also working on two projects, an adaptation of Shadow Country, a novel by Peter Matthiessen, and a movie version of Deadwood. But his days at the racetracks are probably over, because he lives on an allowance of $40 per week.

Addiction to horse races can lead to a person’s financial ruin, as the stories above show. However, gambling on horses today is not limited to the racetracks. Online casinos today are considered well rounded if they offer means of sports betting and betting on horse races, and many of them do. In addition to bonuses, such as those here, online casinos today offer means of betting on horses from home, and as such, become attractive for people who are horse racing enthusiasts. Horse racing has been around for a long time, and horse betting has been the best thing to do at the races since the first horse race. It is safe to assume that the above stories, which are not isolated stories of gamblers who have lost it all on the racetracks, will be repeated again in the future.